1. Field of the Invention
The present invention relates to new and valuable phenyl piperazine compounds and more particularly to 1,4-substituted phenyl piperazine compounds of noteworthy therapeutic utility and to a process of making and using same.
2. Description of the Prior Art
ARCHER in U.S. Pat. No. 3,062,821 discloses 1,4-disubstituted-2-piperazinones of Formula I ##STR1## In said formula R represents lower alkyl;
X and X' represent hydrogen, lower alkoxy, or hydroxyl; and PA1 Y hydrogen or lower alkyl. PA1 R.sub.2 is hydrogen or methyl; PA1 R.sub.3 is hydrogen, alkyl, cycloalkyl, phenyl, naphthyl, alkyl, chloro, or alkoxy substituted phenyl or naphthyl, aralkyl, alkyl substituted aralkyl, or 2-furyl; PA1 R.sub.4 is hydrogen or alkyl; and PA1 R.sub.5 is hydrogen or alkyl. PA1 R' and R" are hydrogen or lower alkyl. These 4-N-substituted-2-ketopiperazines are valuable activators and synergists for insecticidal agents. PA1 R is di-(lower)alkylamino (lower)alkyl, and preferably dimethylamino ethyl, diethylamino ethyl, dipropylamino ethyl, dimethylamino propyl, diethylamino propyl, di-n-propylamino propyl, or lower alkyl substituted by one or two saturated monocyclic heterocyclic rings such as piperidino, pyrrolidino, piperazino, N-lower alkyl piperazino, 3-ketopiperazino, morpholino, or the like, preferably piperidino ethyl, morpholino ethyl, or dimorpholino propyl; PA1 R.sub.1 is lower alkyl with 1 to 3 carbon atoms; and ##STR6## is the group ##STR7## PA1 R.sub.3 is hydrogen or a saturated five- or six-membered heterocyclic ring, preferably the morpholino ring attached by its heterocyclic nitrogen atom to the lower alkyl R.sub.2 ; and PA1 R.sub.4 and R.sub.5 are lower alkyl or, together with the nitrogen atom to which they are attached, form a saturated five- or six-membered heterocyclic ring, such as the pyrrolidino, piperidino, piperazino, or morpholino ring. The piperazino ring may be substituted at its other nitrogen atom by lower alkyl or by hydroxy lower alkyl to represent the N.sub.4 -lower alkyl or N.sub.4 -hydroxy lower alkyl piperazino ring or it may be substituted by a keto group to represent the 3-keto piperazino ring. PA1 a. The N.sub.1 -phenyl lower alkyl substituted 2- or 3-phenyl substituted N.sub.4 -basically substituted 3- or 2-piperazone compounds of Formulas VII or VIII: ##STR9## and b. the N.sub.1 -phenyl lower alkyl substituted 2- or 3-phenyl substituted N.sub.4 -basically substituted piperazine compounds of Formulas IX and X: ##STR10## PA1 Y.sub.1 and Z.sub.1 are hydrogen, halogen, trifluoromethyl; hydroxyl, lower alkoxy, and phenyl lower alkoxy, whereby X.sub.1 is lower alkoxy only if Y.sub.1 and Z.sub.1 are lower alkoxy; PA1 R.sub.1 is lower alkyl with 1 to 3 carbon atoms; PA1 R.sub.2 is lower alkyl; PA1 R.sub.3 is hydrogen or a saturated five- or six-membered heterocyclic ring, said heterocyclic ring being attached by its heterocyclic nitrogen atom to the lower alkyl R.sub.2 ; PA1 R.sub.4 and R.sub.5 are lower alkyl or, together with the nitrogen atom to which they are attached, form a saturated five- or six-membered heterocyclic ring. PA1 1-(4-chloro benzyl)-2-phenyl-4-(diethylamino ethyl)piperazine PA1 1-(3,4-dichloro benzyl)-2-phenyl-4-(diethylamino ethyl)piperazine; PA1 1-[(4-methoxy phenyl)-ethyl]-2-phenyl-4-(diethylaminoethyl)-piperazine; PA1 1-[3-phenyl propyl-(1)]-2-phenyl-4-(diethylamino ethyl)-piperazine; PA1 1-(4-chloro benzyl)-2-phenyl-4-(piperidino ethyl) piperazine; PA1 1-(4-chloro benzyl)-2-phenyl-4-[1,3-dimorpholino propyl-(2)]piperazine; PA1 1-(4-chloro benzyl)-3-phenyl-4-(diethylamino ethyl) piperazine. PA1 Hal is halogen.
Said 1-[2-(phenyl lower alkyl)]-4-lower alkyl-2-piperazinone compounds are useful intermediates in the preparation of compounds of Formula II ##STR2## in which R, X, X', and Y represent the same substituents as given hereinabove. These 1-[2-(phenyl lower alkyl)]-4-lower alkyl piperazine compounds are useful hypotensive agents.
DE BENNEVILLE in U.S. Pat. No. 3,390,139 discloses N-vinyl-2-piperazinones of Formula III ##STR3## in which R.sub.1 is hydrogen, alkyl, cycloalkyl, aralkyl, alkyl substituted aralkyl, diaminoalkyl, or furfuryl;
These compounds are polymerizable or copolymerizable compounds, the resulting polymers or copolymers are useful for many purposes. Higher members of the monomeric N-vinyl-2-piperazinones of Formula III show fungistatic and bacteriostatic activity and are useful for other purposes.
DE BENNEVILLE in U.S. Pat. No. 2,653,153 describes 4-N-substituted-2-ketopiperazines of Formula IV ##STR4## in which R is alkyl, tertiary aminoalkyl, or aralkyl; and
None of these compounds has found any noteworthy application in veterinary and human therapy.